I recently received a message from a student that highlights a struggle, I think, almost everyone has faced at some point.
They wrote: “Vinh, when I meet with strangers, I find it really difficult to come up with questions to ask them.”
It’s a terrifying feeling! Standing there, mind blank, hoping a brilliant topic of conversation will just fall out of the sky.
But here is the truth:
That feeling of “not knowing what to say next” during a conversation isn’t a personality flaw, it is just a lack of preparation.
They say that luck is defined by when preparation meets opportunity. So, instead of hoping you get lucky and the conversation flows, I want you to prepare to be lucky.
Becoming a Better Conversationalist
Mastering the art of conversation is as simple as having a list of five questions in your “Back Pocket” which can be used at any given moment.
Here my 5 personal favourite “Back Pocket” questions that I share with my students to ensure they never run out of things to say:
Question 1. The Classic (With a Planned Response)
The first one is super easy. Everyone does it.
“Hey, how are you going?” (or “Alright mate?” – if you’re British)
Now, you know that by asking this, 99% of people are just going to say, “Yeah, good. Doing well. How are you?”
Most people waste this moment by replying, “Good, thanks.”
🛑Don’t do that!🛑
Have a planned response ready.
- Them: “How are you?”
- You: “Oh, thanks for asking! You know, one of the most exciting things that happened to me today was [Insert Story]…”
All of a sudden, you’ve got the conversation moving. You took a dead-end greeting and turned it into a story.
Question 2. The “Foodie” Question
This is one I absolutely love asking because I am a massive foodie. This is perfect for quick interactions, like if I’m meeting someone in an elevator or waiting in a lobby.
“Hey quick question; have you been to a restaurant that’s really good nearby? I’m trying to explore some new places.“
This is a win-win situation.
- If they know a place: We start talking about food, flavors, and experiences. I win.
- If they don’t know a place: It’s okay. I still got to practice my small talk and break the ice.
Question 3. The “Time-Travel” Questions
These questions depend on your level of comfort. I usually use them if I’m sitting next to someone on a bus or waiting in a line where I know we will be together for at least 10 or 15 minutes.
The Look Back:
“Hey, I’m curious; what’s something interesting that’s happened to you in the past few weeks?”
The Look Forward:
“What are you looking forward to the most in the next 12 months?”
Now, I know what some of you are thinking. “Ah, no Vinh! That feels too weird. I can’t ask a stranger that!”
It feels weird for you. It’s not weird for me.
Why? Because I’ve practiced it. Try it before you judge it. You will be surprised at how open people are when you give them a chance to talk about the good things in their life.
Question 4. The “Wisdom” Question
I am always looking to learn. If I get the sense that the person I’m talking to has some experience or wisdom to share, I’ll go to this one:
“What’s the best piece of advice you’ve been given in the last year?”
This cuts through the surface-level chatter immediately. It signals that you value their perspective and often leads to a much deeper connection than talking about the weather.
Question 5. The “Character” Question
Finally, if you really want to get to know a person, don’t ask about their job.
Asking “What do you do?” usually leads to a rehearsed, boring answer about their profession. I find it is way better to ask:
“What do you do in your free time?”
You learn so much more about a person by understanding their hobbies and passions than you do by asking about their 9 to 5.
Choose Your Own Adventure
When I meet new people, I always lead with the easy, opening questions. But once the door is open, I “choose my own adventure” depending on my mood.
- If I’m hungry? I ask about food.
- If I’m feeling philosophical? I ask about their best piece of advice.
- If I want to know who they really are? I ask about their free time.
The Golden Rule of Becoming A Better Conversationalist:
Don’t hope for a good conversation. Prepare for one.
Ready to take your communication to the next level?
If you want to dive deeper, I invite you to join my Free MasterClass – it’s the perfect primer for anyone looking to lead with more impact.
Or, if you are looking for a comprehensive communication skills transformation, explore my full range of in-person and online courses. Whether you prefer learning from home or joining me in the room, I have a pathway designed to elevate your communication and elevate your stage in life.
